Holiday rentals with a pool in Berkshire County

This property was fantastic. It was great for adults and kids. The inground pool and hot tub were used all day and night. The house had many amenities for everyone. We have 3 grand children, (ages 5-7), the hosts had all kind of spaces and toys for them to utilize. Excellent place for kids inside and out! House was very well appointed and very user friendly. We loved our family time there and would not hesitate to return. Thank you!!!

I think this is the most beautiful air BNB I've ever stayed at. The property is super big and perfect for families. There are a ton of bedrooms and bathrooms and the living area is so beautifully decorated. The kitchen was well stocked and really modern. There's tons of stuff to do right in the home so you don't have to venture away, but if you do you're very close to everything you'd need. The pool was pristine. There were gorgeous fire flies putting on a show for us every night. The view was incredible. We even saw a rainbow on our last day. It was peaceful and private. I highly recommend this place and the hosts. They were super responsive and went above and beyond to accommodate us when we were dealing with some car troubles. Thanks for the incredible stay!

Absolutely beautiful space. Spotlessly clean. Full kitchen amenities plus a little coffee station. Fabulously comfortable beds and living room furniture. Deliciously soft towels. Just an overall great experience and peaceful stay!!

Our group of 10 family members and close friends had a wonderful time at this lovely house. It's large, clean, comfortable, and well equipped for cooking and relaxing together. The instructions were clear and comprehensive. Jay is friendly, knowledgeable, and responsive - in short, an excellent host. Our whole experience gets a big thumbs up!

We had a great time during our stay! It was raining and cold, so while we couldn’t enjoy the pool, the hot tub was wonderful! The house was clean, spacious, and comfortable, which allowed our families to relax and enjoy the beautiful location!

This is the second year we have stayed at Morgan’s home, and it is spacious, welcoming, clean, and very well equipped! This year we had much better conditions than last year (snow!) and walked down the road and skied right on to the mountain. It’s a few minutes, but is not any worse than trying to find a parking space when there are none and walking up all of those steps! It was awesome! Morgan is attentive and communicative and our large family absolutely love staying and can’t wait to come back!

Stayed here with three others for work. The house was clean and well updated. We had no issues and will look to stay here again.

Thank you for a clean and comfortable stay! We were in town visiting family and this was an ideal central location. The pool was a fun addition for our kids plus we were able to turn on the heater ourselves with no issues. Property was exactly as described and it had almost every kitchen gadget for the home cook. There was even a well organized drawer of glass storage containers. Convenient and thoughtful! It’s always quiet and peaceful whenever we visit the Berkshires and this trip was no different.

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

Hamilton is a wonderful host and the area is always beautiful and fun.

This is our second time staying and we loved it even more the second time. Christina was lovely to book with and the unit we were put in had recently been renovated so it was in great shape. You really can't beat this place for a winter family vacation. The space was clean and well appointed. I'm very finicky when it comes to hotel cleanliness, there were a few notes I'd give on the space but overall I was very happy with the space and our overall stay. The staff at Wyndham were very helpful and friendly. We will definitely return again!

We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+

We had a great stay here. It was very close to the ski lifts, and the ski locker was directly across the hall. It made for a very enjoyable and easy skiing experience. Jiminy Peak is a great place to ski at with a variety of trails for all skill levels, and even though it was a school vacation week/weekend, the lift lines were never long. Margaret was very responsive to any questions we had and made the process easy. We loved it!

Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts

We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

We stayed at Renee’s place during a summer festival weekend hosted at the mountain and it was perfect for our needs! Comfy bed, good kitchen set up and a nice place for lounging in between festival events. Would definitely stay here again!